Director of Sales (Health Systems)
About The Position
Join Us at TailorMed – Transforming Healthcare Affordability
Awarded Best in Class in Health Equity 2025
At TailorMed, we’re on a mission to eliminate barriers across the entire medication journey—from affordability to access and adherence. As a pioneering force in healthcare, we’re building a new category that transforms how patients, providers, pharmacies, life sciences, and payers collaborate to ensure every patient receives the treatment they need without delay.
TailorMed is the medication success platform removing every barrier across the patient journey, from access and affordability through adherence and ongoing care. Through a connected network spanning 945+ hospitals, 4,700+ clinics, 3,100+ pharmacies, 100+ life sciences programs, and 6,000+ support programs, TailorMed has supported over 75 million patients and secured more than $7.4 billion in financial assistance since 2020. TailorMed's platform, including TailorMed Core, TailorMed Connect, TailorMed Complete, TailorMed Amplify, and TailorMed Alliance, connects patients, providers, pharmacies, and life sciences companies through one coordinated network designed to reach every patient at every step of their medication journey.
Learn more at tailormed.co
Are you a proven sales leader with a track record in enterprise healthcare SaaS sales? We’re seeking a Director of Sales to drive growth and expand our impact across health systems, IDNs, oncology networks, and specialty pharmacies. In this strategic role, you’ll own a portfolio of enterprise accounts while relentlessly pursuing new business opportunities in the digital health, patient access, and affordability solutions space.
You’ll thrive here if you’re energized by purpose-driven work, skilled at navigating complex healthcare organizations, and motivated by the challenge of exceeding quotas in long-cycle, high-value sales environments. Join our fast-growing team and help shape the future of patient affordability in healthcare.
Requirements
- Demonstrated success in enterprise-level, B2B healthcare SaaS sales, preferably in areas such as patient support services, specialty pharmacy, care coordination, or financial assistance platforms—where navigating clinical and administrative workflows is essential
- Proven track record selling into complex healthcare organizations, including health systems, IDNs, oncology departments, specialty pharmacies, and/or community oncology centers, with experience managing long sales cycles and engaging cross-functional stakeholders
- Understanding of the patient affordability landscape, including exposure to copay assistance programs, foundation support, free drug programs, or reimbursement navigation—ideally through direct collaboration with access, financial navigation, or specialty pharmacy teams
- Exceptional relationship-building, communication, and presentation skills
- Ability and desire to target and develop cold leads and build pipeline
- Knowledge of industry-relevant market research, sales, and negotiating principles
- Strong planning, closing, and multitasking skills
- Ability to learn and adapt quickly
- Enthusiastic with a positive attitude, resilience, and perseverance
- Willing to travel 30-50% of the time